4-Methyl-5-(2-methyl-propenyl)-pyridine-2-carboxylic acid ethyl ester → 5-Isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester

HRID 2037308Notes

Reaction equation

HRID 2037308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:8][N:7]=1)=[O:5])[CH3:2]>C1COCC1.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 670270034-Methyl-5-(2-methyl-propenyl)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 670270295-Isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl esterYield 94.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-5-(2-methyl-propenyl)-pyridine-2-carboxylic acid ethyl ester (1.33 g, 6.06 mmol) in THF (10 mL) and ethanol (10 mL), Pd/C (300 mg, 10% Pd) is carefully added. The slurry is stirred at rt for 15 h under 2 bar of H2. The catalyst is filtered off and the filtrate is concentrated and dried to give 5-isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester (1.27 g) as a colourless oil; LC-MS: tR=0.86 min, [M+1]+=222.10.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customdried

Sources & evidence

ORD record
ord-190cae2ecac240f1aaf7bb11b6a4574e
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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